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Shemales Porn Stories

Becoming his girl (Sissy story by GirlyGay)

FetishShemalesTaboo

In the summer after my eighteenth birthday, I met Nick. He was a thirty-something who lived in our building. My parents had gone for their yearly European trip, and I had been left behind this year because I had college orientation during what would have been the last week of their trip. Mooning and alone, with nothing to do for four whole weeks until my flight up west, I took to the pool to catch some sun. I had not bought new trunks in a while, and so my old ones were riding high on my legs. Nick was already at pool, beer in hand, sitting back in a barca-lounger. His broad, smooth che… Read more

Posted by sissyAlyna 2 years ago 8 3,934 100%

The Rendezvous Pt1 (Sissy Story by CassidyCaine)

FetishShemalesTaboo

Nick looked at the email he'd received from his wife at lunch again as he got ready to leave work. It had been a month since he'd confessed to her his love of dressing up in women's clothing after he'd kept it hidden since they first met. But, Nikki was insistent so he had tried to share that part of him. She had worried he was gay or didn't want her anymore but he'd assured her that wasn't the case. Yet after all that worry, she had emailed him to tell him that tonight she wanted to play with his fantasy and role play a little to see if she could get into it. She had rented a motel room and w… Read more

Posted by sissyAlyna 2 years ago 1 1,550 100%

The Lady Inside by loyalsock

AnalFirst TimeShemales

I looked at the sinuous curves of her body. The long legs, the curling hair. She was built like my fantasy, every inch of her in pale ivory and inky black. Her pumps hugged the delicate curve of her feet—the arch and the heel. Her dress matched in deep crimson and swung light and silky around her narrow hips and broad back. I stared, unsure if what I was seeing was real or just Hollywood smoke and mirrors. When she turned to me and smiled—lovely white teeth glistening behind her red, red lips—I almost fell backward. I was beginning to think she was a mirage brought on by the heat of the Mexica… Read more

Posted by loyalsock 2 years ago 1,033 100%

Nothing Else Matters 1 by loyalsock

AnalHardcoreShemales

About a week had passed since the incident with Casey coming by my work place, trying to blackmail me, by telling my friends I was dating a transsexual. I had talked with Christina about the whole situation, and she had been able to calm me down and help me relax. I had been so pissed off at first, that I couldn't even think clearly at the time. But with Christina's help, I was now seeing things a little more clearly than before, and I had even come to a decision of how I thought I could solve the problem without being f***ed to sl**p with Casey as she was demanding. I would let everyone I… Read more

Posted by loyalsock 2 years ago 1 917 100%

summer vacation

First TimeShemales

hi my name is alex and these is story is about, how i got my first taste of sperm. it was the first week of summer holidays i went to visit my grandmother, who lives in the north. i took the train there, the cart was full first, but after several stops i had it for myself. i was really horny,so i looked around and saw i was really alone. i took my dick out and started jerking it slowly. as the time passed i got at my full size and i was pretty close to cumming. the i heard a whisper behind me "hey boy, need any help" i panicked and tried to hide my dick back into my pants .… Read more

Posted by readyCreampie 2 years ago 2 3,208 93%

Caught and made into a sissy slut

AnalFetishShemales

It was for real this time. No fantasy. Reality. I was dressed up in red: fishnet stockings, g-string, and a babydoll. I was wearing a metal chastity cage that was pulling my clit down, and it was a clit, it only half filled the cage. I had a new cock too - a black face dildo which was double-ended. In my new role, I had to jerk it as I was fucked in my pussy and I was being fucked. She had fucked me so hard that I was completely submissive to her, sucking on my gag with wild abandon, a true sissy slut. It had started earlier that day when I had been caught jerking off to a mixture of cuck… Read more

Posted by andygone 2 years ago 4 7,578 98%

Dominant Sex Therapy

AnalHardcoreShemales

I had to go see a sex ther****t because I was addicted to jerking off. Little did I know she had a surprise waiting for me when i got there. I sat down and she got right to the questions. "So how long have you been jacking off" She asked. I said "about 20 years now" She nodded her head and asked " Do you watch porn when you jerk off?" I said "Yeah every time" She said "Good. How many times a day do you jack off" I said "all depends sometimes once, If i get a really good scene I try to break my mind from cumming too fast so it can be, 4-5 times a day." She said "Wow that's a lot of masturbat… Read more

Posted by michneo 2 years ago 3 6,636 81%

my date with jennycumslut part two

First TimeShemalesTaboo

The second part of my story about my date with Jennycumslut. This memory will be burned in my mind forever and thinking about it drives me wild to know I did what I always fantasized about! Hopefully this will make you cum hard... I left off that I had just made plans with Jenny to see her later that evening. I was out for a nice paced walk in the park close to my apartment at the time we had made plans so I hurried back home. After drenching of sweat from hurrying home since I was to meet her in less than a hour I quickly showered and didnt have time to shave my pubes down. Me and her t… Read more

Posted by redhotnailpolish 2 years ago 1 1,469 89%

Gary's Dressup Sissy

AnalFirst TimeShemales

When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games. One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One mov… Read more

Posted by palmorr 2 years ago 17 4,096 100%

The last time I was a slut for cock

AnalGay MaleShemales

This is an account from my diary about the last time that I was a total slut for cock, before I realised that there was power in being dominant. Went over to see Peter yesterday, it was about 8pm when I left his house but I didn’t have to worry about rushing home. It was nice being with Peter again, he’s taught me so much the past year and he loves me in feminine clothes but he wouldn’t let me take the dress that I’d worn for him home. He let me go home wearing the bra, pants, stockings and suspenders though, it felt lovely wearing them when riding my bike. I felt so happy having spent th… Read more

Posted by angelatvdom 2 years ago 4 4,041 96%

Old man fantasy

First TimeMatureShemales

I have always been aroused by horny old men,I always wanted to be exploited by a group of old horny men until one day when i got this job that required me to take care of a 66 y.o gentleman. He seemed so nice and since it has been my passion to serve other men i accepted the job without thinking twice.Things went well and we got along just fine..he was really funny and we became close friends very fast. One day he called me and told me that he must speak with me face to face so that he can share a problem that he had for years with me,I rushed over to his place worried that something may hav… Read more

Posted by cutecdkiss 2 years ago 7 3,855 100%

Vicky's Pink Diary 04

Gay MaleShemalesTaboo

My head is spinning now, and as my uncle slowly pulls my panties down, I close my eyes dreading my fate! I watch as he pulls my case out from under the bed. He takes a key out of his trouser pocket and unlocks the padlock. "My god, how long have you had a key?!" "Vicky, surely you remember losing a key a little while ago. It fell out of your jeans when your stepmother pulled them out of the washing machine. She didn't notice, but I did. Now I don't want to bring the other you up, but I did wonder why you would have a key in your jeans." I knew I'd lost one of the keys, but I ne… Read more

Posted by sparkyking 2 years ago 2,589 100%

Vicky's Pink Diary 03

Gay MaleShemalesTaboo

So here I am waiting for my Uncle to come home for his tea, wearing Donna's knickers! Vicky's wardrobe is quite sparse, due to having just one locked suitcase hidden under my bed. I'm lucky that my stepmother is roughly the same size as me, and a total slut! Probably the only thing I like about Jenny is her clothes, she dresses like a girl half her age, and I know for a fact she shags around. I know my friend Sean has had a few narrow escapes from my stepmother. Then one day when I ask him about the way they smile at each other, he owned up. So I now know that they have fucked, I finally got i… Read more

Posted by sparkyking 2 years ago 2 2,355 100%

Male to female transgender. Had no idea!

AnalShemalesTaboo

This is a true story. This was a time in my life where I was sort of a bitter person. This story is geared more about the things that led up to my encounter. This was a result of a series of events led up to this point in my life. Let's begin with the basics. I was in the military. I enlisted because I had one full time job and two part time jobs and still had trouble making ends meet. I was seriously overworked and my wife refused to get a job. So logically, I weighed out my options and decided to enlist into the military. It would be one full time job with a slew of benefits. Once I graduate… Read more

Posted by fortworthfitness 2 years ago 30 4,543 99%

Wife and Sissy invited to a party

FetishHardcoreShemales

My wife and I were invited to some friends’ house on a beautiful estate in TX for a weekend party. While we were both well aware of the debauchery that could occur at the event, we had no idea how much participation we would both play. We were just getting off the plane to meet our driver when my wife handed me a slutty little maid outfit, and told me to go into the bathroom in the airport and change before we got out of the terminal. I did as she asked and then tried to walk out without anyone noticing but too many people in the airport to hide from as I only attracted more attention. When… Read more

Posted by moeclitty 2 years ago 8 3,847 93%

Jake and sexy Tgirl Amanda were next on our "

AnalGroup SexShemales

So after we went out with Pete and Becky all day Jet Ski's, Diving, and sneaking off for some impromptu blowjobs or a quicky, Alex and I decided that we'd ask Pete and Becky if they'd mind if we brought Jake and Amanda into our group. We described them to them, and they were hooked. That evening at dinner Alex took it upon herself to make the first move. She sent over some drinks, and they came over to our table and that's where this story begins. Amanda asked if we were swingers, when I spoke up and told her that even better than that, we're all bi swingers. Her jaw dropped and he… Read more

Posted by SpicySide69 2 years ago 6 2,752 100%

Deflowered at 17...Part 1 (ENGLISH VERSION)

FetishFirst TimeShemales

Many friends, some of them curious and excited by my (recently discovered) Polaroid pictures made at the seaside (with stockings) when I was 17 years old, asked me to tell the story associated to them. Someone also pointed out, "but if in one of your stories you talk about your first man -see story “my first man”- after having been “initiated” by a trans, then who was actually your first man? " First of all, let me say that I can assure you that my stories are not fancy, they are absolutely true. I can change some details, names, situations, ... but I do not not invent anything. Anyone who… Read more

Posted by AngelicaTrav 2 years ago 11 4,260 100%

Deep throat Made Easy

First TimeGay MaleShemales

Deep throat Made Easy -reposted fro menext Here for the first time ever are simple and explicit instructions on how to deep throat a penis. Position is important; you'll want to in position where you can extend and straighten your neck by slightly tilting your head back. This helps line up your throat with your mouth allowing the penis to slide in deep. The best position for beginners is with the receiver lying on his back with the giver lying on the stomach along side. You can prop yourself up on your elbows. The penis must be THOROUGHLY LUBRICATED! I can't stress this enough. An… Read more

Posted by bigdaddycoolzz 2 years ago 5 2,915 100%

''What's a man to do'' Pt

AnalFetishShemales

We reached the fun chamber and I unlocked the door and told the lady's to go in and get to know each other while I went and fetched some glasses and a two bottles of red and a bottle of bubbly. I returned to find the girls siting on the edge of the bed chatting and giggling like two school girls. It surprised me that Elke hadn't this hot little thing between her legs licking her pussy out. Usually my wife doesn't waste time chatting when she has an itch that needs scratching. I locked the door, not really because I didn't anyone walking in on us, after all it was a sex party, but because a… Read more

Posted by guru6969 2 years ago 2 1,986 86%

Pai-chan’s long walk home

FetishFirst TimeShemales

School-gurl Pai-chan took the short-cut home from school, through the Sakura sweet smelling woods one Friday after class. The trail went past an old hut and as she approached it, a masked man jumped out from behind her, grabbed her by the arms and slipping a ball-gag into her mouth, d**g the sexy gurl into the hut. There was a dirty, stained mat in the hut and her a*****or threw Pai-chan onto it. He lit a cigarette, his eyes glinting through the mask as he watched her struggle uselessly against the bonds. “No… Read more

Posted by tuckpussypeachpie 2 years ago 6 2,888 100%